GB1451844A - Spirolactone and 17a-dicarboxyethyl steroid derivatives processes for their preparation and processes for converting them into related compounds - Google Patents
Spirolactone and 17a-dicarboxyethyl steroid derivatives processes for their preparation and processes for converting them into related compoundsInfo
- Publication number
- GB1451844A GB1451844A GB545274A GB545274A GB1451844A GB 1451844 A GB1451844 A GB 1451844A GB 545274 A GB545274 A GB 545274A GB 545274 A GB545274 A GB 545274A GB 1451844 A GB1451844 A GB 1451844A
- Authority
- GB
- United Kingdom
- Prior art keywords
- processes
- preparation
- spirolactone
- dicarboxyethyl
- converting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 title 1
- 229960002256 spironolactone Drugs 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical group 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- -1 Steroid carboxylates Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Catalysts (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1451844 Steroid carboxylates and spirolactones ROUSSEL-UCLAF 6 Feb 1974 [6 Feb 1973] 5452/74 Heading C2U The invention comprises compounds II, II<SP>1</SP>, IV and V infra and their preparation and conversion to compounds C by the routes shown R is C 1-4 alkyl; R 2 is H or Me; R 3 is Me or Et; M is alkali metal. Compounds VII are the subject of Specification 1,451,845. Reagents: VII#VIII and IX#II: e.g. chloranil or DDQ; VII#XI and VIII#II: CH 2 (CO 2 R) 2 /base; II#II<SP>1</SP>: alkali then acid; II<SP>1</SP>#IV or V: alkali metal base: II or II<SP>1</SP>#C: heat (with water in the case of II), e.g. by autoclaving with toluene at 120-140 C./2À5-3À0 kg./cm.<SP>2</SP>.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7304058A FR2216276B1 (en) | 1973-02-06 | 1973-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1451844A true GB1451844A (en) | 1976-10-06 |
Family
ID=9114389
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB545274A Expired GB1451844A (en) | 1973-02-06 | 1974-02-06 | Spirolactone and 17a-dicarboxyethyl steroid derivatives processes for their preparation and processes for converting them into related compounds |
| GB113476A Expired GB1451845A (en) | 1973-02-06 | 1974-02-06 | Spiro-oxirane steroid derivatives and processes for preparing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB113476A Expired GB1451845A (en) | 1973-02-06 | 1974-02-06 | Spiro-oxirane steroid derivatives and processes for preparing them |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3919198A (en) |
| JP (2) | JPS5940840B2 (en) |
| AT (1) | AT344924B (en) |
| BE (1) | BE810644A (en) |
| CA (1) | CA1025436A (en) |
| CH (1) | CH594702A5 (en) |
| DK (1) | DK136827B (en) |
| ES (2) | ES422922A1 (en) |
| FR (1) | FR2216276B1 (en) |
| GB (2) | GB1451844A (en) |
| IE (1) | IE40282B1 (en) |
| LU (1) | LU69329A1 (en) |
| NL (1) | NL179384C (en) |
| SE (1) | SE416950B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2344286A1 (en) | 1976-03-16 | 1977-10-14 | Roussel Uclaf | NEW DERIVATIVES 17-SPIROSULTINES, THE CORRESPONDING G-HYDROXY ACIDS, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS A MEDICINAL PRODUCT |
| US4155906A (en) * | 1977-12-02 | 1979-05-22 | G. D. Searle & Co. | Process for preparing steroidal 3-oxo-4,6-dienes such as 17-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acidγ-lactone |
| DE2950832C2 (en) * | 1979-12-18 | 1983-03-17 | Hoechst Ag, 6000 Frankfurt | Ready-to-use injectable aqueous solutions of the alkali salts of canrenoic acid and furosemide |
| TWI283245B (en) * | 2002-03-22 | 2007-07-01 | Upjohn Co | Processes to prepare eplerenone |
| DE102005049393B4 (en) * | 2005-10-15 | 2019-08-08 | Kennametal Widia Produktions Gmbh & Co. Kg | Method for producing a coated substrate body, substrate body with a coating and use of the coated substrate body |
| CN108033989A (en) * | 2017-12-28 | 2018-05-15 | 广西万德药业有限公司 | The preparation method of canrenone |
| CN110028542A (en) * | 2019-05-17 | 2019-07-19 | 山东宝利甾体生物科技有限公司 | The clean preparation method of canrenone |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1089788A (en) * | 1965-07-07 | 1967-11-08 | Parke Davis & Co | Process for the production of steroidal lactone compounds and intermediates thereof |
-
1973
- 1973-02-06 FR FR7304058A patent/FR2216276B1/fr not_active Expired
-
1974
- 1974-02-01 US US438602A patent/US3919198A/en not_active Expired - Lifetime
- 1974-02-05 BE BE140581A patent/BE810644A/en unknown
- 1974-02-05 LU LU69329A patent/LU69329A1/xx unknown
- 1974-02-05 SE SE7401495A patent/SE416950B/en not_active IP Right Cessation
- 1974-02-05 CH CH158574A patent/CH594702A5/xx not_active IP Right Cessation
- 1974-02-05 CA CA191,777A patent/CA1025436A/en not_active Expired
- 1974-02-05 ES ES422922A patent/ES422922A1/en not_active Expired
- 1974-02-06 GB GB545274A patent/GB1451844A/en not_active Expired
- 1974-02-06 GB GB113476A patent/GB1451845A/en not_active Expired
- 1974-02-06 JP JP49014628A patent/JPS5940840B2/en not_active Expired
- 1974-02-06 NL NLAANVRAGE7401657,A patent/NL179384C/en not_active IP Right Cessation
- 1974-02-06 AT AT92274A patent/AT344924B/en not_active IP Right Cessation
- 1974-02-06 IE IE227/74A patent/IE40282B1/en unknown
- 1974-02-06 DK DK62674AA patent/DK136827B/en not_active IP Right Cessation
-
1976
- 1976-01-16 ES ES444369A patent/ES444369A1/en not_active Expired
-
1982
- 1982-03-19 JP JP57042991A patent/JPS5850240B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2216276A1 (en) | 1974-08-30 |
| SE416950B (en) | 1981-02-16 |
| JPS5850240B2 (en) | 1983-11-09 |
| JPS49109366A (en) | 1974-10-17 |
| SE7401495L (en) | 1974-08-07 |
| LU69329A1 (en) | 1974-09-25 |
| JPS5940840B2 (en) | 1984-10-03 |
| AT344924B (en) | 1978-08-25 |
| BE810644A (en) | 1974-08-05 |
| AU6521074A (en) | 1975-08-07 |
| ES444369A1 (en) | 1977-05-16 |
| NL7401657A (en) | 1974-08-08 |
| DK136827C (en) | 1978-05-08 |
| ES422922A1 (en) | 1976-09-16 |
| IE40282L (en) | 1974-08-06 |
| ATA92274A (en) | 1977-12-15 |
| NL179384C (en) | 1986-09-01 |
| CA1025436A (en) | 1978-01-31 |
| IE40282B1 (en) | 1979-04-25 |
| US3919198A (en) | 1975-11-11 |
| JPS57176999A (en) | 1982-10-30 |
| GB1451845A (en) | 1976-10-06 |
| FR2216276B1 (en) | 1976-11-05 |
| CH594702A5 (en) | 1978-01-31 |
| NL179384B (en) | 1986-04-01 |
| DK136827B (en) | 1977-11-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1443680A (en) | Manufacture of hydroxylated chloesterol derivatives | |
| GB1441101A (en) | Reagents for the assay of cardenolide glycosides and aglycones | |
| GB1445236A (en) | Process for the preparation of 25-hydroxycholesterol and 3- alkanoyloxy derivatives thereof and pregnanes useful therein | |
| GB1451844A (en) | Spirolactone and 17a-dicarboxyethyl steroid derivatives processes for their preparation and processes for converting them into related compounds | |
| GB1491296A (en) | Steroidal precursors of 1alpha-hydroxy-vitamin d3 | |
| GB1242194A (en) | A new oestratriol and a process for its manufacture | |
| ES8506326A1 (en) | Estrane and androstane derivatives, process for their preparation and pharmaceutical preparations containing them | |
| GB1368006A (en) | 4alpha,7alpha-carbonyl-5-cyano-17-hzydroxy-3-oxo-5beta,17alpha- pregnane-21-carboxylic acid ypsilon-lactone | |
| JPS5352690A (en) | Preparation of coenzyme q | |
| GB1455220A (en) | ||
| SE7605799L (en) | METHODS OF PRODUCING STEROID-CARBOXYLIC ACID-LACTONS | |
| GB1463850A (en) | 4-deoxy-4-oxoerythromycin b derivatives | |
| GB1462718A (en) | Digoxin complexes | |
| GB1450693A (en) | Beta-3-oxo-7alpha-acylthio-17beta-hydroxy-4-androsten-or estren- 17alpha-yl- propionic acidderivatives | |
| GB1364194A (en) | Acetals and ketals of 20 21-dihydroxy-pregnane compounds | |
| GB1529249A (en) | 21-acetals and mixed acetals of steroidal 21-aldehydes intermediates and methods of preparation | |
| GB1381207A (en) | Ketones | |
| GB1504134A (en) | 2-bromo-6beta-fluoro-pregnane compounds | |
| GB932325A (en) | Estrane derivatives | |
| GB1504132A (en) | 6beta-fluorosteroids of the pregnane series | |
| GB1152180A (en) | delta<8(14)>-Steroids | |
| GB1206816A (en) | Novel 4-oxa steroids, processes for their preparation and conversion into other steroids, and the steroids thus produced | |
| GB1512543A (en) | Cholestane derivatives and their preparation | |
| GB1324613A (en) | Epoxy estranes and process for their preparation | |
| JPS5432696A (en) | Preparation of microorganism floculant noc-1 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |